Amino sugar

(biochemistry) A monosaccharide in which a non-glycosidic hydroxyl group is replaced by an amino or substituted amino group; an example is D-glucosamine.

A sugar in which one or more nonglycosidic hydroxyl groups is replaced by an amino or substituted amino group. The most abundant example is D-glucosamine (2-amino-2-deoxy-D-glucose) [see illustration].

Structural formula of D-glucosamine (α-pyranose ring form).

A linear polymer of N-acetyl-D-glucosamine is widely distributed as chitin, the exoskeletal material of arthropods. The glycoproteins of higher animals, which are components of the proteoglycans of cartilage and skin, consist of polysaccharides that are generally sulfated and have N-acetylated glucosamine or galactosamine alternating with a uronic acid.

Amino sugars are important constituents of glycoproteins and oligosaccharides involved in biological recognition. Amino sugars of the greatest structural diversity are found in microorganisms as constituents of cell walls, in antigenic carbohydrates produced at the cell surface, and as antibiotic substances secreted from the cell. Streptomycin is the first demonstrated example of numerous amino-sugar-containing antibiotics produced notably by Actinomycetes (bacteria). See also Chitin; Glycoprotein; Oligosaccharide; Polysaccharide.

Glucosamine

Sialic acid

In chemistry, an amino sugar contains an amine group in place of a hydroxyl group.^[1] Derivatives of amine containing sugars, such as N-acetylglucosamine and sialic acid, while not formally containing an amine, are also considered amino sugars.

Aminoglycosides are a class of antimicrobial compounds that inhibit bacterial protein synthesis. These compounds frequently contain amino sugars (but in some cases contain aminocyclitols).

Common examples of amino sugars include:

• N-Acetylglucosamine
• Galactosamine
• Glucosamine
• Sialic acid

References

1. ^ Amino sugar, Encyclopedia of Science & Technology Online

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